Substituted amides

ABSTRACT

Substituted amides as new chemical compounds. These compounds have been found to be useful in the control of bacteria.

United States Patent Blake Related US. Application Data Division of Ser. No. 92,898, Nov. 25, 1970, Pat. No. 3,706,796.

Inventor:

us. (:1 252/107, 252/117, 252/548, 260/558 D 1m. (:1 Clld 9/50 Field of Search .4252/106, 107, 117,548; 260/558 D [111 3,870,646 [451 Mar. 11, 1975 References Cited UNITED STATES PATENTS 3,455,940 7/1969 Stecker 260/559 3,666,668 5/1972 Klausner 252/l07 X Primary Examiner-Richard D. Levering Assistant Examiner-4. A. Nelson Attorney, Agent, or Firm-Howard C. Stanley; N. E. Willis; J. E. Maurer [57] ABSTRACT Substituted amides as new chemical compounds. These compounds have been found to be useful in the control of bacteria.

10 Claims, No Drawings SUBSTITUTED AMIDES This is a division of application Ser. No. 92,898 filed Nov. 25, 1970, now US. Pat. No. 3,706,796.

This invention relates to a novel class of organic chemical compounds. More particularly, this invention is concerned with novel substituted amides which have been found to possess useful and unexpected biological activity.

The novel compounds of this invention have the formula wherein n and m independently are or 1 provided that the sum of n m is at least 1;

a and b independently are 0 or 1 provided that the sum ofa h is at least I; and X X X and X, are independently selected from the halogens chlorine and bromine.

The substituted amide compounds of this invention wherein m is l and n is 0 can be readily prepared by reacting an appropriate dihalogenated benzyl amine with an appropriate dihalogenated benzoyl chloride. Such a reaction is illustrated by the following equation:

The substituted amide compounds of this invention wherein m is 0 and n is 1 can be readily prepared by reacting an appropriate dihalogenated aniline with an appropriate dihalogenated phenylacetate. Such a reaction is illustrated by the following equation (the illustrative phenyl acetate is a phenyl phenyl acetate):

The substituted amide compounds of this invention wherein both In and n are I can be readily prepared by reacting an appropriate dihalogenated benzylamine with an appropriate dihalogenated phenylacetate. Such a reaction is illustrated by the following equation (the illustrative phenyl acetate is a phenyl phenyl acetate):

0H1 -0 CHzNH-z x. g I X.

in the above illustrative preparation reactions a. b. X X X and X have the same meanings as defined hereinabove.

ln practicing the preparations of this invention, it is preferred to carry out the reaction in the presence of an inert organic solvent. Suitable solvents include benzene, toluene, xylene, the chlorinated benzenes, ethyl ether, propyl ether, tetrahydrofuran, and the like.

The reaction temperatures employed in the preparation of the compounds of this invention will vary from room temperature to the reflux temperature of the reaction mixture. The specific temperature employcd in any given preparation will be primarily dependent upon the particular reactants used therein. It should be noted that, although the presence of an inert organic solvent is preferred, it is not essential to the preparation of the compounds described herein.

The invention will be more fully understood by reference to the following examples which are set forth herein for the purpose of illustration only and which are not to be construed as limiting the scope of this invention in any manner.

EXAMPLE I Analysis Calcd. for C,. H,,Cl NO C 46.06; H 2.49 Found: C 45.87; H 2.49

EXAMPLE 2 N-(3,4-Dichlorobenzyl)-3,5-dichloro-2' hydroxyphenylacetamide 4 3,4-Dichlorobcnzylaminc (2 g., 0.0114 mole) was added to phenyl 3,5-dichloro-2-hydroxyphenylacetate (3 g., 0.01 mole) and the mixture became quite warm. The mixture was diluted with 1,2,4-trichlorobenzene (20 ml.) and heated to l-l90C. for 2 hours. The white product (4.5 g.) was precipitated by the addition of petroleum ether and recrystallized out of toluene, gave a product that had a melting point of l44l45C. (corr.)

Analysis Caled. for H CI N0 47.53; HV 292 Found: 2

EXAMPLE 3 Analysis Calcd. for C H CI NO C, 45.60; H, 2.8l Found: C, 45.70; H, 2.74

EXAMPLE 4 N-(3.4-Dichlorophenyl)-3,5-dichloro-2- hydroxyphenylacetamide A mixture of phenyl 3,5-dichloro-2-hydroxyphenylacetate (3.0 g., 0.01 mole) and 3,4-dichloroaniline (2.0 g., 0.0123 mole) in 1,2,4-trichlorobenzene (25 ml.) was heated with stirring for 4.5 hours at l74l 80C. The cooled reaction was diluted with petroleum ether to precipitate 4.3 g. of product. The product recrystallized out of diluted methanol after decolorizing with charcoal and had a melting point of 193-l94C. (corr.)

Analysis Caled. for C H ChNO e H, .4 Found: H, .4

In representative standard dilution tests the substituted amide compounds were found to be effective against Slupliylm'occux am'eur at the dilutions shown in TABLE I (which shows the highest dilution at which no growth of Slap/1ylococ'c'us aureus is observed).

TABLE 1 Compound of Example Highest Dilution (lzX) Similar activity is displayed by the other and different substituted amides of this invention.

Relatively small amounts of these substituted amides in a detergent soap composition have been found to yield effective antiseptic detergent soap compositions. Amounts as low as 0.1 to 1 percent by weight based upon the weight of the detergent soap have proved satisfactory in some instances. However, it is preferred to employ these substituted amides in amounts in the order of l to 3 percent by weight based on the detergent soap. While larger amounts may be employed. as for example. up to l() percent by weight. the upper limit will be determined by practical considerations. Various colors, antioxidants, perfumes, water softeners, emollients and the like may be included where desirable in detergent soap compositions containing the new substituted amides. The term soap or "detergent soap as used herein is employed in its popular or ordinary sense, i.e., those cleansing compositions prepared from an alkali metal compound such as potassium or sodium hydroxide and a fat or fatty acid. both saturated and unsaturated.

While the invention has been described herein with regard to certain specific embodiments. it is not so limited. It is to be understood that variations and modifications thereof may be made by those skilled in the art without departing from the spirit and scope of the invention.

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as fol- 'lows:

H OHM cms-pw-wna...

wherein,

n and m independently are 0 or 1 provided that the sum of n m is at least 1;

a and 17 independently are 0 or I provided that the sum of a bis at least I: and provided that when nis0ais0;and

X X X and X are independently selected from the halogens chlorine and bromine.

2'. An antiseptic detergent composition as defined in claim 1 wherein n is 0.

3. An antiseptic detergent composition as defined in claim 1 wherein m is 0.

4. An antiseptic detergent composition as defined in claim 1 wherein the sum of m and n is 2.

5. An antiseptic detergent composition as defined in claim 1 wherein a is 0 and b is l.

6. An antiseptic'detcrgent composition as defined in claim I wherein b is 0 and a is l.

7. An antiseptic detergent composition as defined in claim 1 wherein the compound is N-(3,5-dichloro-2- hydroxybenzyl)-3,4-dichlorobenzamide.

8. An antiseptic detergent composition as defined in claim 1 wherein the compound is N-( 3.4- dichlorobenzyl-3,5-dichloro-2- hydroxyphenylacetamide.

9. An antiseptic detergent composition as defined in claim 1 wherein the compound is N-(3.5-dichloro-2- hydroxybenzyl)-3,5-dichloro-2- hydroxyphenylacetamide.

10. An antiseptic detergent composition as defined in claim 1 wherein the compound is N-(3,4- dichlorophenyl)-3,5-dichloro-2- hydroxyphenylacctamide. 

1. An antiseptic detergent composition comprising a detergent soap and 0.1 to 10 percent by weight based on the detergent soap of a compound of the formula
 1. AN ANTISEPTIC DETERGENT COMPOSITION COMPRISING A DETERGENT SOAP AND 0.1 TO 10 PERCENT BY WEIGHT BASED ON THE DETERGENT SOAP OF A COMPOUND OF THE FORMULA
 2. An antiseptic detergent composition as defined in claim 1 wherein n is
 0. 3. An antiseptic detergent composition as defined in claim 1 wherein m is
 0. 4. An antiseptic detergent composition as defined in claim 1 wherein the sum of m and n is
 2. 5. An antiseptic detergent composition as defined in claim 1 wherein a is 0 and b is
 1. 6. An antiseptic detergent composition as defined in claim 1 wherein b is 0 and a is
 1. 7. An antiseptic detergent composition as defined in claim 1 wherein the compound is N-(3,5-dichloro-2-hydroxybenzyl)-3,4-dichlorobenzamide.
 8. An antiseptic detergent composition as defined in claim 1 wherein the compound is N-(3,4-dichlorobenzyl)-3,5-dichloro-2-hydroxyphenylacetamide.
 9. An antiseptic detergent composition as defined in claim 1 wherein the compound is N-(3,5-dichloro-2-hydroxybenzyl)-3,5-dichloro-2-hydroxyphenylacetamide. 